


Dean Winchester Gay Ships

by wistfulwinchester



Category: Supernatural
Genre: Bisexual Dean Winchester, Bottom Castiel/Top Dean Winchester, Bottom Dean Winchester, Daddy Dom Benny Lafitte, Fluff and Smut, M/M, Plot What Plot/Porn Without Plot, Porn, Rough Sex, Smut, Top Castiel/Bottom Dean Winchester, Top Dean Winchester, Violence
Language: English
Status: In-Progress
Published: 2021-03-02
Updated: 2021-03-12
Packaged: 2021-03-14 20:07:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 6,984
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29797206
Author URL: https://archiveofourown.org/users/wistfulwinchester/pseuds/wistfulwinchester
Summary: Dean Winchester Gay ships (nsfw) (no wincest, don't even think about it) 18+ onlyChapter 1: Dean/Benny in purgatoryChapter 2: Destiel having fluffy sexChapter 3: Destiel having rough sexChapter 4: Destiel but top!dean for onceChapter 5: Dean/Alastair in hell
Relationships: Benny Lafitte/Dean Winchester, Castiel/Dean Winchester
Comments: 2
Kudos: 36





	1. Ditch the Brain, Darling (Benny/Dean)

**Summary for the Chapter:**

> Dean and Benny get close in purgatory....very close.

"Get out of your head, Dean," Benny whispered into Dean's ear in his low drawl. His breath was hot on Dean's neck as he grabbed Dean's hips and pulled his ass against him. Benny began to grind into Dean slowly.

Dean tried his best to 'get out of his head'. His mind was spinning with a million thoughts and protests. Benny was a vampire, Dean was (supposedly) straight, they were in purgatory with a threat behind every tree, everything about this was unnatural and wrong. And what would Sam think? Dean had no doubt Sam would accept the whole ~gay~ thing, as that seemed to be his style. But with a monster?? Despite his brother's words, Dean knew Sam had never fully forgiven him for killing Amy Pond. And now here he was doing the exact thing he'd beat the shit out of Sam for doing if he ever caught him.

"Dean," came that soft cajun accent again. It was scolding and teasing and made Dean's heart quicken. "I said ditch the brain, darling." Benny reached around Dean's waist and began to rub the crevice where his thigh connected to his pelvis. Dean's next exhale shuddered out of him and he barely held back what would have been an embarrassing moan. His head dropped back into Benny's shoulder and he closed his eyes, his brow creased and his lips parted slightly, his mind temporarily distracted from its panic.

"Need I remind you, it was you who kissed me first," Benny said, nibbling the lobe of Dean's ear. Dean's mind flashed back to the night before. Him and Benny had finally found a quiet place to get a few hours of sleep. Dean had propped himself against a tree and closed his eyes when Benny had startled him by reaching over with a large hand and pulling a twig from Dean's hair, then allowed his fingers to brush down the hunter's temple and stubbled cheek. Dean's heart rate had quickened and when his eyes fluttered wide open Benny's face had been inches from his. And from there- sure Dean had leaned foreward and pressed their lips together but to imply that he had actually initiated the kiss wasn't exactly fair-

Just then, Benny's hand travelled a little to the side and began to palm Dean's swollen cock through his jeans. Dean panted in short gasps and his hips bucked slightly into Benny's hand involuntarily, any snarky arguments that had formed in his mind vanished suddenly. Benny chuckled and kissed the side of Dean's head. "Come on, darling," he spun Dean around and pressed him into a nearby tree. He kissed Dean gently at first. Tenderly pressing his lips into Dean's and running his hands up and down Dean's sides and back over his t-shirt. Then he gradually picked up the pace and took fistfuls Dean's t-shirt, pulling himself closer to the slightly taller man. He caught Dean's bottom lip in his teeth and pulled it gently.

Benny pulled away and Dean's eyes fluttered open, his heart racing, wondering what would come next. "Gonna make you feel so good, baby boy," Benny murmured, caressing Dean's face. "Is that what you want?" Dean nodded slightly, pushing away the stampede of panicked thoughts that threatened to come crashing back. He DID want this. No use denying it to anyone, especially not himself. His body sent currents of electricity under his skin to chase Benny's fingertips and lips wherever they touched. Benny's sharp blue eyes took him in hungrily in a way that made Dean feel so.... WANTED. Needed. Dean bucked his hips again and nodded more certainly.

"Say it, darling," Benny whispered, grinding his clothed erection into Dean's. "I want to hear you say it. Do you want this?"

"Yes," Dean whimpered, the desperation in his tone causing him to cringe slightly.

"Yes....sir?" Benny tested, a wicked grin creeping onto his lips.

Dean's breath caught in his throat as Benny's demand rushed straight to his dick, causing it to somehow harden even more. "Yes, sir" he gasped, abandoning all hesitation. He leaned forward to kiss Benny again but Benny turned his face at the last second.

"Not so fast, baby boy," he chuckled. "Gonna give you a treat." He dropped to his knees and Dean's heart lept. "Daddy's gonna show you a few tricks and then you're gonna return the favor, yeah?" Dean nodded, his eyes wide and eager. Benny didn't move, still staring at Dean expectantly.

"Yes, sir," Dean gasped, understanding. Benny chuckled again and carefully unzipped Dean's jeans.

"Do me a favor and take off that t-shirt"

Dean pulled it over his head and cast it to the side as Benny pulled down his jeans. Benny licked his lips at the sight of the large bulge behind Dean's boxers. A damp spot of precome had already started to spread and Benny growled softly. Benny gripped Dean's hips firmly and held him against the tree as he kissed along the bulge from the base to the tip, eliciting a stream of tiny gasps and moans that would have embarrassed Dean if he wasn't so overcome with arousal and need. Benny stopped his ministrations and gazed up at Dean, blue eyes flashing as he pulled down Dean's boxers. Dean's long length sprung up and Dean hissed at the exposure to the cold air. Benny eyed Dean hungrily in a way that drove the hunter wild. He tried to buck his hips again but Benny held him firmly against the tree.

"Now, now," Benny murmured. "Patience, darling." He leaned in to kiss Dean's thighs and abdomen, leaving his leaking cock untouched. "There he is," Benny purred as Dean began to gasp and writhe under his touch. "There's my baby boy. There's my good boy." Benny gently affirmed between each kiss and Dean whined in response. "Ready for Daddy to suck that pretty cock, darling?"

"Yes sir," Dean pleaded, "Please."

"Anything for you, baby boy," Benny purred. Then he took the tip of Dean's dick in his mouth, sucking gently. Dean panted, electricity shooting up his length and into his abdomen. Fireworks exploded in Dean's brain and he writhed against the tree, hands desperately searching for something to grasp and finding nothing. Benny suddenly sank lower, taking Dean's entire length and swallowed around it. Dean let out a loud, obscene moan and his head fell back against the tree. 

"Yes, yes, yes" he chanted.

Benny pulled back, grinning. "Shhhhh, quiet now," he corrected. "I love your noises, darling, but you might trick a leviathan into thinking you're a wounded and easy snack." Dean gulped and scanned the area anxiously. Nothing that he could see and he became distracted again as Benny went back to work.

This time Dean tried to keep it down. Biting back louder moans turned them into grunts and whines and the excess trapped energy caused him to buck despite Benny's strong hands holding him down. "S-s-sir" Dean gasped after a few minutes of this. "I'm gonna- ohhhh"

Benny pulled off and gazed up at the hunter who was lost in pleasure. "Cum for Daddy, Dean." He growled and went back to his cock with such sudden ferocity that Dean couldn't hold back the loud moans that streamed from his mouth as he came down Benny's throat in intense pulses.

Benny swallowed and then stood up and took Dean's mouth with his, sliding his tongue into Dean's mouth and letting him taste himself. Dean gave himself over limply to Benny's arms and mouth. Benny pulled away finally and whispered into Dean's ear "let's change locations, just in case any of them monsters heard you banshee-screaming there. Then it's your turn."

*comment for part II !!!*


	2. I Love You Too, By the Way (Destiel)

**Summary for the Chapter:**

> Sweet, sexy, fluffy destiel

Dean sat on his knees on the foot of the bed, staring in awe at the sight before him. Castiel lay spread out, his head throw back against the headboard, eyes closed, full lips parted, and his hand slowly stroking his cock. Dean subconsciously thrust his hips slightly and his lips moved in barely perceptible motions as he allowed himself to imagine his lips around that girthy dick. Cas let out small pants and quiet moans. "You're so beautiful," Dean breathed, his pupils blown with lust.

Castiel's eyes fluttered open and he gave Dean a soft half-smile. "Come here," he murmured, and Dean didn't need to be told twice. He crawled on top of Cas and pressed his lips to his. Cas put his arms around Dean and traced his fingers up and down the hunter's back. "Dean," he whispered tenderly. "Dean. You're mine, beloved. All mine."

"Yeah," Dean whispered into Cas' mouth. "Yeah baby, all yours." Dean Winchester had never seen himself falling in love. To him, love had always meant weakness. Something for the monsters to hurt you with. But Cas- something was different about Cas. Something gentle and irresistible. Dean had once joked that Cas must have used his jedi-mind tricks on him. Of course, Cas had not understood and it had become a whole ordeal of explaining the reference to him (to little avail, "I have no such tricks," the angel had said.) But something about Castiel's cluelessness in pop culture was charming to Dean. Cas was precious. Dean didn't want to fight this feeling anymore.

"Where'd your mind go," Cas asked, and Dean realized he had been spaced out for a few seconds. 

"Just thinking about you," Dean answered, then slyly added "and wishing you'd let me suck that pretty dick."

Cas gave another half smile. "It's for you," he said, bumping his erection into Dean's thigh and kissing him again.

Dean swallowed thickly and smiled. "Thanks," he kissed his way down Castiel's body. Three kisses along his jaw, then one right below his ear, then two down his neck. Collar bone, chest, nipple, sternum. Then right above his naval. Then right below it. Cas was writhing slightly under Dean's attentions, his hips bucking in small motions.

Dean began to kiss Cas' thighs, nearing his cock but never quite touching it. Cas whimpered and threaded his fingers through Dean's light brown hair. "Dean," he moaned pleadingly in that gravelly voice that shot straight to the core of Dean's heart. He knew what his angel wanted and he was incapable of denying him anything.

"Alright, Cas. Alright, baby," Dean whispered into Castiel's warm skin before taking his cock in his mouth. Cas' mouth fell open into a soft "o" shape as Dean swirled his tongue around the head of his dick. Dean then pushed down and took in as much of the length as he could, groaning softly around it. He pumped up and down in steady rhythm, encouraged by his angel's moans. Dean opened his eyes and looked up towards Cas who's deep blue eyes connected with his instantly and widened.

"I love you," Castiel breathed, his tone broken. Dean responded by speeding up and sucking harder. "ohhhhhh," Cas arched his back slightly and then lifted hips slightly. "Dean, Dean, Dean," Dean loved hearing his name on Cas' lips like this and took the swollen cock even deeper, letting it hit the back of his throat. Cas cried out loud and long, and then to Dean's surprise, pushed Dean's mouth away, causing drool to dribble down his chin.

"Wha-" Dean's confused protests where cut off by Cas pulling his face up and kissing him hard.

"Fuck me, Dean," Cas growled, holding Dean's face in his hands and staring hungrily into the hunter's green eyes. "Please, I've been thinking about it for days. Since the first time. Please."

"Yes," Dean breathed. "Yes, Cas, anything." They had only done this once before, about a week ago and it had been sloppy and awkward and Dean had left feeling less-than adequate. But Cas had been thinking about it every day? And craving it? A softness crept into Dean's chest and he closed his eyes to soak it in for a moment. He blindly reached out to where he knew Cas was watching him, probably confused, and pulled his lover against his chest tightly. "I love you too, by the way."

"Because of the sex," came Castiel's matter-of-fact tone. Dean's brow furrowed and his eyes shot open. How could he think that? And then he saw Cas's eyes twinkling humorously.

"Did you just tell a joke?"

"Maybe you're rubbing off on me," Cas smiled. "I know you love me, Dean. You don't even have to say it. I knew it even before you did. Now...fuck me."

Dean obeyed, crashing his lips into the angel's and pushing him back against the bed. He reached for the lube sitting on the bedside table and spread some on his fingers. Then reaching down, his eyes widened. "You already prepped yourself?"

Cas smirked, "like I said, I've been... thinking about this quite a bit. It's not the same, though." Dean bit his lip, then stuck two fingers in just to be sure. Then a third. "Dean, do I need to ask again?" Castiel grumbled impatiently.

"No," Dean slicked his cock with lube and pressed his tip against his lover's entrance. He slowly pushed in, letting out a low moan at the pressure and the heat. Cas moaned with him as Dean bottomed out. They both waited a moment, adjusting, and then Dean began to grind his hips. He nestled his face into the crook of Castiel's neck and allowed himself to be lost on the pleasure and the overwhelming love.

Cas mewled loudly when Dean found his prostate and Dean made sure to hold that angle. Soon the pair were grinding into each other, picking up the pace. Dean panted as he felt his stomach twist in that familiar feeling. "Cas, I'm not going to last much longer."

Cas reached between them and began stroking his dick in time with Dean's thrusts. "Okay, Dean" he murmured into Dean's hair. "Alright, come on. Cum for me." Cas' gentle words melted Dean and pushed him over the edge. He came with a groan, and Cas followed suit seconds later.

Dean pulled out but didn't roll off of Cas' chest. Cas didn't ask him to. Instead he wrapped his arms around the hunter and held him as their breathing steadied and the endorphins flooded their systems. Eventually Dean fell asleep, snoring softly into Castiel's neck. Castiel smiled and closed his eyes, relishing the moment.


	3. Not Michael's (Destiel)

**Summary for the Chapter:**

> Alt ending to Castiel beating the shit out of Dean in that alley in season 5.

**Notes for the Chapter:**

> // rough sex, Castiel is pissed, top cas, bottom dean,

Cas grabbed Dean by the shirt collar and threw him against the dirty wall of the alley. "what, are you crazy?" Dean spluttered. Cas had appeared out of nowhere. Cas pulled him back and threw him again, the pair stumbling into nearby trash cans. 

"I rebelled for this?" Cas growled, punching Dean across the face. His eyes were blue fire and furious. Dean felt the pit in his stomach turn ice cold. Cas threw him against the wall again. "So that you could surrender to them?" Cas punched Dean in the stomach. Then again. Then again. 

"Cas, please," Dean pleaded. He could fight back, but the guilty rock in his stomach knew Cas was right. Knew that he was wrong. But what other option did he have? 

Cas ignored the plea and slammed him against the wall again. "I gave EVERYTHING for you. And this is what you give to me?" Cas pulled him away from the wall and punched his face again. Dean stumbled, but regained his footing. Just in time for Cas to kick him in the chest. Dean fell backwards onto the slimy ground of alley. The smell of cheap beer and urine assaulted his nose. Sirens wailed in the distance.

Dean coughed and gazed up at Cas who was towering above him now, murder and hatred in his eyes. His jaw was clenched along with his fist. Cas was going to kill him. The sirens were getting closer. "Do it," Dean dared him, angrily. Who was Cas to pretend he was so holier-than-thou. There was no hope left. Saying yes to Micheal was their only hope. "JUST DO IT," he screamed. Cas released his fist and approached the hunter. Dean's heart jumped, he hadn't actually expected Cas to do it. Cas touched him and Dean winced, bracing for whatever being smited felt like.

When nothing happened, Dean opened his eyes. He was no longer in the alley, but on the nearly-equally dirty floor of a motel room. He scrambled to his feet. Cas was standing, staring out the window with his back turned. The room was dark, only Cas' silhouette was visible, but he was trembling. "...Cas?" Dean said tentatively, slowly getting to his feet. Cas snapped his fingers and the lights came on. He whirled on his heel and faced Dean. There were tears on his face but his mouth was still pressed into a tight, angry line. 

Cas pointed a shaking finger at Dean, "millennia after millennia after millennia," He began, his voice shaking. "I was faithful. I was obedient. Even when my mind told me to do otherwise. Even when I grew jealous of humans and their free will and their joy. I never ONCE considered betrayal. They were my family, Dean. But for you? I sacrificed everything I had ever known. EVERYTHING."

"Cas-" 

"YOU DON'T SPEAK," Cas roared, he grabbed Dean by the throat and shoved him roughly against the wall, cutting off Dean's oxygen. "Don't you speak to me. How dare you? HOW DARE YOU" Dean grunted and writhed, trying to loosen Castiel's grip on his neck. Cas held on for a few more moments, glaring as he squeezed his hand tighter and tighter and then finally released. Dean gasped hoarsely and fell to his knees.

He held up his hands palm forward out to Cas, trembling. "I don't have a choice, Cas," he croaked. "I have to say yes."

Cas' mouth turned up in disgust and he shook his head. "We will find another way," he said levelly. "It was you who taught me that." Then his voice turned sorrowful. "I loved you," he whispered. "I love you."

Dean's heart nearly stopped cold. Something in Cas' tone told him he meant more than the brotherly affection they had already confessed to. Or was it his imagination? He had imagined this moment a lot but he had never imagined it like this. "Cas, what-" he stumbled on his words. "What do you mean by that?"

Cas turned to him, pain written over every inch of his face. "Like....Adam and Eve," his voice was rough. "But you betrayed me."

"I'm sorry," Dean's voice quivered. "Cas, I'm sorry. He reached up and grabbed Cas' hand. Cas didn't move, his hand hung limply. "Please... Cas please forgive me. I love you too."

Cas was angry again at once. He pulled his hand away, "Don't say that to me." He turned and began to walk back to the window. Dean hung his head, tears rolling down his face. But then Cas suddenly changed course, pulled his face back up and kissed him roughly. Dean's eyes widened briefly but then he sunk into the kiss. Cas was so rough. Tearing at his split lips with his teeth and holding Dean's bruised face tightly. But Dean didn't want him to stop. He reached up to put his hands on Castiel's neck and torso but Cas slapped his hands away. The angel pulled away from the kiss. "Take off your clothes."

Dean scramble to his feet and obeyed, stripping down to nothing. "Now get on the bed," Cas growled. "Hands and knees." Dean gulped but did as Cas demanded. Cas stood behind him silently, and then a palm came down hard on Dean's ass, Dean hissed. Then the palm came down again. And again. And again. Cas continued until Dean cried out "Cas stop, please stop." He did.

"Okay," the angel murmured, running his hands up and down the hunter's back, "Okay." He kissed Dean between the shoulder blades, a surprisingly tender action after the ceaseless beating Dean had endured since the alley. A warmth spread out from the kiss and coated Dean's entire body, healing every inch. "I'm sorry, Dean." Cas stood there, blue eyes sad and a frown creasing his brow.

Dean blinked away his shock and chuckled, "not like I didn't deserve it," he said, rolling into his back, "and besides it was...uh... kinda hot." He paused, not knowing how Cas would react to that. Cas just stood there. "C'mon man, what are you thinking right now?"

"I am thinking I would like to kiss you," Cas said, "but I don't know if you would want me to, considering I just, as you would say 'beat the shit out of you.'"

Dean laughed, "you can kiss me, Cas" he said softly.

Cas did not hesitate, he was on top of Dean in an instant, kissing him passionately. He slipped his tongue into Dean's mouth and explored it excitedly, then moved to kiss down Dean's jaw and neck. Dean let out small gasps and pants, his hips rocking of their own accord. He tugged at the shoulders of Cas' trench coat and Cas shrugged it off, while lapping at Dean's nipples and making him whimper. Dean threw the trench coat aside and began to fumble awkwardly with the buttons on Castiel's shirt. Cas grumbled at being interupted and snapped his fingers. Instantly all of his clothes were removed and folded tidily on the bedside table. "That's a neat trick," Dean smiled, "You'll have to use it more often."

"Yeah if you're so lucky," Cas growled and sat up on his knees, still straddling Dean who was sitting so his face was lined up with Cas' cock. Cas said nothing, just stared, but Dean knew what to do. He opened his mouth and Cas thrust his dick into the hunter's throat. Dean gagged slightly, but kept his composure. Castiel thrust steadily into Dean's mouth, breathing heavily.

After a few minutes Cas began to moan and grunt softly and he pulled away, leaving drool and precum smeared on Dean's chin, the man's eyes wide and lust-blown, lips still slightly parted. Castiel bit his lip, "you look so good like this," he pushed Dean back into the bed and hovered over him, kissing him greedily. "I'm going to fuck you now. Make you mine. You're mine, do you understand? You belong to me."

Dean nodded, whimpering at Cas' words and the possessive look in his eyes. Cas disappeared briefly and then reappeared before Dean had a chance to wonder what happened. A bottle of lube was in his hand. Dean didn't ask where it came from because almost instantly the cap was off, Cas' fingers were coated and one was circling Dean's entrance. How was he so FAST?

"Mine," Cas growled as he stuck one finger, causing Dean to moan. He pumped slowly at first and then picked up speed. He added another. "Not Michael's. Not Heaven's. Not God's." He added a third. "MINE."

"Yes, yeah. Yeah, Cas," Dean whimpered pathetically. "Yes, please, Cas, please." Castiel's finger's brushed Dean's prostate and the man screamed out in pleasure. Cas removed his fingers causing Dean to whine. The angel spread lube over his cock and slowly lined up with Dean's hole. He hesitated, barely brushing it with the end of his cock. Dean writhed impatiently.

"Say my name, Dean." Cas commanded. "You don't deserve this. Beg me for it."

"Please, Cas."

"My name, Dean."

"Please, Castiel. Please. I need you. I need you, please, Castiel. Please." Dean was whining and writhing and pleading in ways he would never admit to another soul. But here with just him and Castiel, nothing felt more right.

Castiel pushed in and Dean let out a long moan. After settling for a moment, Castiel began to thrust at a vicious pace. Dean moaned uncontrollably, his head lolling from side to side. "Dean," Castiel said lowly and gently. Dean looked at the angel. He was gazing down at Dean as he moved in and out of him. His face was cool and commanding. "Hold my eyes," he demanded and Dean did. Unfocused green meeting the clear ice blue.

"Cas I'm gonna cum," Dean whimpered, his cock twitching against his stomach. 

"You don't deserve to cum," Castiel said calmly.

"No, no Cas please. Please I need to."

"Hmm," Castiel said thoughtfully, slowing down his thrusts to an excruciating snail's pace. "Maybe I am feeling surprisingly generous. Maybe I want to see you come undone. But not until I cum first, do you understand." Dean nodded, transfixed by this new, domineering Castiel. Castiel sped up again and Dean closed his eyes, focusing all his energy on NOT cumming.

"You're so pretty, Dean," Castiel hissed. Castiel's pants became ragged and his thrusts sloppy. "Hold still," he demanded. "Open your mouth." He pulled out of Dean and jerked himself off onto Dean's mouth and chin, groaning deeply. "Good boy," he praised. "Jerk yourself off for me, baby." Dean obeyed, reaching down and only managing a few strokes before he came across his stomach, panting. Castiel's eyes widened and he leaned down to lap up the fluid. When he was done, he snapped and everything was cleaned and they both had their boxers on.

Dean felt a sleepiness overtake him but he fought it to say "Cas I'm not saying yes to Micheal."

Castiel wrapped his arms around the exhausted hunter. "I should hope not," he murmured, kissing the side of the man's head.

"I love you, Castiel."

"I love you, Dean."


	4. Am I Right? (Destiel again)

**Summary for the Chapter:**

> What Dean SHOULD have done instead of kicking Cas out in season 9.

**Notes for the Chapter:**

> // top dean, "gadreel" sam, anal sex, blowjobs, (evidently I suck at writing top!dean my apologies)

"My time with April was very educational," Cas said in his gravelly voice.

"Yeah I'm sure getting killed is... something," Sam said awkwardly, neither him or Dean knowing exactly what Castiel meant.

"And having sex," Cas said.

Dean choked, "you had sex with April?" A strange flicker of emotion filled his chest suddenly. What was that? Anger? ...Jealousy? Cas just nodded. Dean cleared his throat and tried to shake it off. "So....did you have protection?" He asked.

Cas frowned, not seeing the relevance of the question. "I had my angel blade," he answered, hesitantly.

Dean stuttered, then turned to Sam "oh he had the angel blade," he smirked, still fighting that bitter feeling under his ribcage.

"In any event, I now see how difficult life can be and how well you two have led it," Cas said. "I think you'll be great teachers."

Dean's mind instantly wandered to the things he'd like to teach Castiel. "Thanks, Cas." He said awkwardly. Cas walked away to get another burrito and Dean turned to Sam and laughed, trying to come across as light hearted. Sam just rolled his eyes.

Suddenly his eyes glowed blue and his posture became stiffer. Dean tensed. "He can't stay," Ezekiel said. "He will bring the angel's down on us. Yes he's warded but he was warded when April found him." Dean opened his mouth to argue but Ezekiel cut him off and held up a finger. "I will not argue about this. Either Cas goes or I do. And you know Sam isn't strong enough for me to leave his body." Sam's eyes glowed blue again and his posture returned to normal.

Sam cleared his throat. "Anyway, I'm going to run into town and grab some food. Cas is about to eat us out of house and home." Dean stared, still trying to catch up with what just happened, his heart sinking. "Dean did...did you hear me?" Sam waved a hand in front of Dean's face.

"Uh...yeah. Good call," Dean cleared his throat.

"Okay...see you in a bit then." Sam turned and headed up the bunker stairs towards the exit.

Dean's gut twisted. He looked over at Cas who was innocently munching a burrito. He couldn't do this to him. Cas NEEDED them. But Cas for Sam's life wasn't a trade he could argue with. It wasn't an option. Dean walked over to Cas and sat on the edge of the table.

"Hey...listen buddy...um..." Dean faltered as wide blue eyes stared up at him, trustingly. Dean's eyes wandered to Castiel's full lips, slightly parted. Dean swallowed and fidgeted. A thousand alternatives raced through his head. Things he'd like to stay instead of the inevitable  
~you can't stay here~. 

"Yes, Dean?" Cas said, his brow becoming worried. Without thinking, Dean leaned forward and took Castiel's face in his hands, pressing his lips hard against the ex-angel's. Cas dropped his burrito onto the table, gasping.

"I'm sorry, I'm sorry," dread filled Dean's stomach. He wouldn't have to send Cas away if he chased him away forever by kissing him out of the blue. But before that thought could go very far Cas was tangling his fingers through his hair and kissing him back. Dean whimpered in relief and put his arms around Cas' waist. The pair sunk into the kiss.

Cas pulled his hands down and began running them up and down over Dean's t-shirt under his flannel. Then tentatively his hands slipped under the t-shirt too. Dean felt himself relaxed under the touch of Cas' fingertips. He pulled the ex-angel's hips against his and began to grind gently, feeling Castiel's dick hardening along with his.

"Cas let's-" Dean gasped as Cas grabbed his ass suddenly with a wicked smile on his face. "Let's go somewhere else. My room." Cas nodded and Dean grabbed his hand and led him to to the carefully organized room. "Um...what do you want, Cas?"

Cas frowned, "I want to have sex with you, Dean."

Cas' matter-of-factness usually made Dean laugh but this time it just caused his chest to swell with joy. "Okay, uh good," He said awkwardly. "I meant meant more like, um...how far do you want to go?"

Cas furrowed his brow again, "Dean you know I don't understand much yet-"

"Okay, okay," Dean wiped his palms on his jeans. "We'll just take it slow. Tell me if you want me to stop, okay?" He reached out to Cas again and then stopped when the man didn't answer his question. "Okay, Cas?"

"Yes, okay," Cas said impatiently.

Dean smiled and brought Cas' mouth back up to meet his. He pulled down the zipper of the hoodie and pulled it off Cas'. Then pulled off the t-shirt. Dean's eyes wandered to the enochian tattoo on Castiel's lower ribs. Cas noticed his gaze.

"I had to for practical purposes," he said "I understand if you don't like it..." His voice trailed.

Dean laughed, "what? Cas I was admiring it." He pulled him in for another kiss. "All tattoos are sexy," he whispered into Cas' mouth.

"Really?" Cas asked, "Let me see yours." He tugged on Dean's shirt. Dean quickly shed his layers and stood before Cas. Cas stared at the devil's trap tattoo on Dean's chest and licked his lips. "Yes," he said, "I understand what you mean." He traced his fingers over it, and then allowed them to go lower. And lower. Then his fingers traced over the bulge in Dean's jeans. Cas palmed it and Dean exhaled softly, beginning to pant.

"Take off your clothes," the hunter said breathlessly, quickly beginning to undo his belt buckle. Cas followed suit and soon the men stood before each other, hungrily taking in each other's bodies with their eyes. Dean guided Cas to the bed and laid him down on his back. Then he placed his hands on the other man's thighs and brought his lips near the throbbing red cock. He let his breath tease for a moment until Cas began the writhe under him. Then Dean took his tip in his mouth and sucked gently, swirling his tongue around the head. Cas moaned.

Dean took in more and more of Castiel's length until he had reached the base. He sucked up and down and Cas' moans became louder and filthier. Dean felt his own cock twitching, begging for contact. He pulled off Cas and glanced up at his wide, eager eyes. His heart fluttered and he smiled. "You're beautiful, Cas," he murmured.

"I could say the same about you, Dean." Cas replied, his eyes softening in a way that melted Dean's insides. Dean inhaled slowly, then reached for the drawer in his bedside table where he kept his lube. 

"Cas remember to tell me if you need me stop," he said, nervously. "It's really no big deal if you do, I promise."

"I understand, Dean. I will tell you, I promise."

"Okay then," Dean spread the lube on his fingers and began to trace them over Cas' entrance. Cas ground his hips up slightly. His lips were slightly parted. As Dean gently slide a finger in, Cas gripped the sheet in tight fists.

"Dean-" he grunted. Dean froze and began to retreat but Cas shook his head "No, please don't stop." Dean hesitated, but then continued, going even slower than he had been. He got on finger in and wiggled it gently, lubing Cas. Slowly he added a second. He began to thrust them and Cas rewarded him with delicious little moans. Crooking his fingers slightly, he brushed the bundle of sensitive nerves and wailed with pleasure so loudly it made Dean grateful Sam wasn't home. Dean added a third finger and a fourth and worked the man until he felt properly convinced he was ready.

Without removing his fingers, Dean used his left hand to squeeze lube over his cock and spread it over the hard surface. Then in he removed his fingers from Cas and lined his dick up with his entrance. "Cas, tell me-"

"-if I want you to stop. Dean I know." Cas interupted, growling. "Please, Dean, I need you." That was enough for Dean, he thrust in, his own moans mixing with Castiel's. Cas wrapped his legs around Dean's waist and threaded his fingers through Dean's hair. "Dean, I'm-"

"Come on, baby," Dean whispered, the pet-name slipping out unwittingly. Cas groaned and came in pulses between their stomachs. Dean wasn't far behind. He felt the familiar sleepy euphoria wash over him as he rolled over to lay beside Cas. Cas looked up at him, blue eyes soft. Then he tentatively moved to put his head on Dean's shoulder. Dean shifted and put his arm around the ex-angel's shoulders, pulling him close. 

"That was even better than with April," Cas murmured. "I didn't know it was possible."

"I guess practice makes perfect," Dean smiled. He felt Cas inhale, preparing to reply but just then the men heard the squeak of the door to the bunker opening. Dean's heart froze, remembering the earlier conversation with Zeke. "Cas stay here," he said, sharper than he meant to.

"Why?" Cas asked, proping himself up on his elbows.

"Will you just do as I say for once," Dean snapped, grabbing his robe and throwing it on.

"Dean-" but Dean had already left the room, slamming the door behind him.

"Zeke!" He yelled

"Who?" Sam asked, but then straightened, his eyes glowing. "Dean. Is Castiel gone?"

"No and he's not going anywhere." Dean growled. "Go ahead and ditch Sam if you insist, we'll figure something else out. We always do. But I'm gonna guess you're not strong enough to leave either. Am I right?"

Ezekiel's lips pressed together in an angry line. "Why do you insist on protecting Castiel. He may be the very one to bring harm to your brother, not me."

"I said am I right?" Dean shot.

Ezekiel said nothing, glowering.

"That's what I thought."


	5. Little Boy (Dean/Alastair)

**Summary for the Chapter:**

> Alastair finds creative new ways to torture Dean in hell

**Notes for the Chapter:**

> // consent issues, orgasm denial, dildo, Dean is tied up, mild torture elements

Dean lay beaten beyond recognition. Nothing left of what once made him human. Flesh barely cleaning to broken bones. The demons surrounding him laughed and snapped their fingers, restoring him completely and they walked away, leaving Dean chained naked to the metal bedframe, the bars that usually held a mattress digging into his back. Dean closed his eyes and focused on relishing these few seconds of relatively pain-free rest before Alastair came in with his proposition. He steeled himself to say no again. He would not torture other souls to spare himself, though the temptation grew daily. Day 724. Or was it 723? He was beginning to lose track. Only an eternity to go.

"Dean," Alastair's nasally voice came. The demon was still in the shadows, out of sight.

"No," Dean said.

"Dean, you haven't even heard what I have to say," Alastair's voice pouted.

"I don't need to," Dean gritted back. "Go to hell."

"Oh, we're here, Dean. I just wanted to know if you'd like to add some pleasure to that pain." Alastair stepped out of the shadows. He was completely naked. Dean awkwardly looked back towards the ceiling (if you could call the space between two endless black cliffs extending into the sky forever a 'ceiling'). "Don't be shy, little boy," Alastair cajoled, his voice like honey. "It's your lucky day. I've chosen you to be my toy for the night."

Alastair crossed to Dean and put his lips against his ear, "Beats the meat slicer," he whispered, leaving damp condensation on Dean's skin. Dean gulped as Alastair's fingers traveled down his bare chest and then dug into his thighs. "So soft," he murmured. He carefully reached and wrapped his fingers delicately around Dean's cock which was hardening rapidly (to Dean's shame). "You like this, huh little boy?"

"No," Dean grunted.

"You haven't been touched like this in...what is it? Nearly two years, huh?" Alastair gentle tugged Dean's length up and down. "And after near constant pain, not even the pleasure of eating or sleeping..." Alastair exhaled shakily, "this has got to feel.... incredible..."

Dean clenched his jaw to hold back a moan as Alastair tightened his grip. The demon was right. Dean felt like a virgin again with how intense the pleasure was. But he wouldn't let any of it show. He still had a little pride left.

"I'm gonna make you scream a different way tonight, baby," Alastair purred. "Make the torture afterwards that much more unbearable."

Dean barely held back a cry as Alastair suddenly put his mouth around his dick and sucked HARD. His back arched involuntarily and he writhed. The demon swallowed around his cock. Then did it again. And again. And again. Demon's didn't need to breath. Dean grunted and Alastair pulled off with a pop.

"Oh little boy, give in to me. It will make this so much easier." Alastair kissed Dean's inner thighs every few words. "And what are you afraid of? It's not like anyone will find out. This is hell, Dean. Eternity. There are no more secrets here. There is no shame in finding pleasure where you can. And this is the only place you will ever find pleasure ever again." Alastair took Dean down his throat again. Dean finally let out a whimper and the demon chuckled around 

"There we go," he purred. "There we go little boy." He snapped his fingers and a long red dildo appeared in his hand. He snapped again and Dean felt a strange sensation, he struggled against the chains slightly. Alastair reached two fingers into Dean's magically prepped ass. Perfect" he grinned. "You truly are a specimen, Dean."

He held the dildo to Dean's lips "lube that up for me, would you, baby?" Dean got the impression that it was going in him, lubed or not, so he parted his lips. Alastair pushed it roughly down Dean's throat causing the hunter to choke. "Oooh," Alastair growled, his hand traveling to his own length. "That's it, baby." He tugged on his remarkably long cock. 

After a few moments, Alastair pulled the dildo away, leaving Dean gasping. He lined the thick plastic cock up with Dean's hole and pushed it in. The tip brushed against Dean's protate and he moaned freely, his pride abandoned on the charred floor of hell. Alastair the turned around and took Dean's cock in his mouth again, lining up his own in front of Dean's mouth. Dean clenched his jaw and turned his face. He would do a lot of things but he would NOT 69 a demon. His defiance earned him teeth scraping up his dick and he yelled, quickly changing his mind. Alastair's dick slipped into his mouth and Dean sucked gently.

Dean closed his eyes and pretended it wasn't Alastair. He HAD missed this, even if he hadn't had time to consciously acknowledge it. The pleasure of sex. The feeling of a dick in his mouth. The feeling of a hot wet mouth around his. His mind went to other men he had fucked. He moaned slightly around Alastair's dick and the demon suddenly got off and turned around.

Alastair reached behind himself and fidgeted with something for a second. Then he revealed a plug he had pulled out of himself and grinned at Dean wickedly. Wordlessly, he grabbed Dean's hard cock and lined it up with his hole. He sank down on it, slowly, and Dean let out a loud moan. "You like that, little boy?" Alastair panted, he ground down on Dean's hips causing the dildo in the hunter's ass to shift and press into his prostate. He did it again and again. Grinding hard and moaning. Dean let out a stream of high-pitched whimpers, the pleasure overwhelming his senses.

"There he is, there you are," Alastair preened breathlessly. "Almost there, baby. Are you ready?" A few more rolls of his hips and Alastair came with a groan, painting Dean's chest with white stripes. "Now cum, baby. Cum inside me." Alastair squeezed his muscles around Dean's cock and then pulled off of him suddenly. Dean gasped and bucked his hips but Alastair just laughed.

"This is hell, after all, little boy," he smirked. "Now..." He grabbed a red-hot fire poker that was hanging with several other torture instruments on the wall. "Come with me and help me torture souls and maybe I'll let you cum next time." Dean spat, glowering. Alastair shrugged "okay," he plunged the poker into Dean's chest.


End file.
